Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates

Chang Woo Cho; Jong Rock Kong; Michael J. Krische

doi:10.1021/ol049600j

Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates

Chang Woo Cho, Jong Rock Kong, Michael J. Krische

University of Texas at Austin

Research output: Contribution to journal › Article › peer-review

198 Scopus citations

Abstract

Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem S_N2′-S _N2′ mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80% yield and 56% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution.

Original language	English
Pages (from-to)	1337-1339
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	8
DOIs	https://doi.org/10.1021/ol049600j
State	Published - 15 Apr 2004

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title = "Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates",

abstract = "Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem SN2′-S N2′ mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80\% yield and 56\% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution.",

author = "Cho, \{Chang Woo\} and Kong, \{Jong Rock\} and Krische, \{Michael J.\}",

year = "2004",

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doi = "10.1021/ol049600j",

language = "English",

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pages = "1337--1339",

journal = "Organic Letters",

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T1 - Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates

AU - Cho, Chang Woo

AU - Kong, Jong Rock

AU - Krische, Michael J.

PY - 2004/4/15

Y1 - 2004/4/15

N2 - Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem SN2′-S N2′ mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80% yield and 56% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution.

AB - Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem SN2′-S N2′ mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80% yield and 56% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution.

UR - https://www.scopus.com/pages/publications/2542448981

U2 - 10.1021/ol049600j

DO - 10.1021/ol049600j

M3 - Article

C2 - 15070331

AN - SCOPUS:2542448981

SN - 1523-7060

VL - 6

SP - 1337

EP - 1339

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates

Abstract

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